Shoes

What shoes to wear with shorts

Im 29, and I think I dress nicely, but I never know what kind of shoes to wear with shorts. I dont think sneakers look good, and I dont like the sandals look. What do you recommend?

Loafers are casual, and they go with shorts, with or without socks. I think a traditional penny loafer is a good shorts look. Id avoid those low-cut Italian jobs—the dreaded low-vamp loafer—that show your instep. Theyre too O. J. Simpson. For years I wore Sperry Top-Siders, boat shoes, and they, too, work with shorts. They arent the greatest walking shoes in the world, but you can get similarly styled shoes that have a little more thickness to the sole. And, of course, if you want to go for that jet-set look, theres always the Tods driving shoe. Again, not a great walking shoe, but if youre out motoring around they look good, and they come in a lot of colors. Theres no reason you cant wear lace-up shoes with shorts, as long as theyre not too bulky or too dressy; forget the wing-tip brogues. The absolute worst choice is some kind of boot. If youre climbing a mountain, suit yourself, but if youre just hanging out youre going to appear a little too Crocodile Dundee.